1,8-bis(6'-hydroxy-4'-methyl-biphenyl-3'-yl)naphthalene | 1334226-15-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 1,8-bis(6'-hydroxy-4'-methyl-biphenyl-3'-yl)naphthalene
• 英文别名: 1,8-bis(6'-hydroxy-4'-methylbiphenyl-3'-yl)naphthalene；1,8-Bis(6'-hydroxy-4'-methylbiphenyl-3'-yl)naphthalene；4-[8-(4-hydroxy-2-methyl-5-phenylphenyl)naphthalen-1-yl]-5-methyl-2-phenylphenol
• CAS: 1334226-15-1；1334226-16-2；1334229-19-4；1334229-20-7
• 化学式: C₃₆H₂₈O₂
• 分子量: 492.617
• InChiKey: DVBDXFXOJGNZEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  38
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,8-bis(6'-hydroxy-4'-methyl-biphenyl-3'-yl)naphthalene 在 sodium t-butanolate 作用下， 以 乙腈 为溶剂， 生成 C₃₆H₂₆O₂^(2-)*2Na⁽¹⁺⁾
  参考文献：
  名称：

  Enantioselective recognition of amines with an atropisomeric 1,8-bisphenolnaphthalene

  摘要：

  1,8-Bis[5'(2'-hydroxy-4'-methylbiPhenyl)]naphthalene, 2, was prepared from 1,8-dibromonaphthalene and 4-methoxy-2-methylphenylboronic acid in four steps with 51% overall yield. The axially chiral anti-isomer of 2 is stable to racemization at room temperature and the free energy of activation for the conversion of the anti-isomer to the syn-form was determined as 110.0 kJ/mol at 77.1 degrees C. At submillimolar concentration, enantiopure 2 can be used as circular dichroism sensor to detect a wide range of chiral amines. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.07.001
• 作为产物：
  描述：

  4-甲氧基-2-甲基苯硼酸 在 potassium phosphate 、 四(三苯基膦)钯 、 三溴化硼 、 N,N,N-trimethylbenzenemethanaminium dichloroiodate 、 溶剂黄146 、 zinc(II) chloride 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 72.5h， 生成 1,8-bis(6'-hydroxy-4'-methyl-biphenyl-3'-yl)naphthalene
  参考文献：
  名称：

  Enantioselective recognition of amines with an atropisomeric 1,8-bisphenolnaphthalene

  摘要：

  1,8-Bis[5'(2'-hydroxy-4'-methylbiPhenyl)]naphthalene, 2, was prepared from 1,8-dibromonaphthalene and 4-methoxy-2-methylphenylboronic acid in four steps with 51% overall yield. The axially chiral anti-isomer of 2 is stable to racemization at room temperature and the free energy of activation for the conversion of the anti-isomer to the syn-form was determined as 110.0 kJ/mol at 77.1 degrees C. At submillimolar concentration, enantiopure 2 can be used as circular dichroism sensor to detect a wide range of chiral amines. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.07.001

文献信息

• Atropisomeric 1,8-bisphenolnapthalenes and their use in enantioselective recognition and asymmetric synthesis
  申请人：Wolf Christian

  公开号：US09085511B2

  公开（公告）日：2015-07-21

  This invention related to atropisomeric 1,8-bisphenolnaphthalenes and derivatives thereof of the general formula (I): which are useful in resolution of enantiomers, enantioselective recognition and asymmetric synthesis.

  这项发明涉及到对映异构体1,8-双酚萘及其衍生物，其化学式为(I)，可用于对映体分离、对映选择性识别和不对称合成。
• ATROPISOMERIC 1,8-BISPHENOLNAPTHALENES AND THEIR USE IN ENANTIOSELECTIVE RECOGNITION AND ASYMMETRIC SYNTHESIS
  申请人：GEORGETOWN UNIVERSITY

  公开号：US20140128637A1

  公开（公告）日：2014-05-08

  This invention related to atropisomeric 1,8-bisphenolnaphthalenes and derivatives thereof of the general formula (I): which are useful in resolution of enantiomers, enantioselective recognition and asymmetric synthesis.

  本发明涉及一般式(I)的异构体1,8-双酚萘及其衍生物，这些化合物在对映体分离、对映选择性识别和不对称合成中有用。
• [EN] ATROPISOMERIC 1,8-BISPHENOLNAPTHALENES AND THEIR USE IN ENANTIOSELECTIVE RECOGNITION AND ASYMMETRIC SYNTHESIS<br/>[FR] 1,8-BISPHÉNOLNAPHTALÈNES ATROPISOMÈRES ET LEUR UTILISATION EN RECONNAISSANCE ÉNANTIOSÉLECTIVE ET SYNTHÈSE ASYMÉTRIQUE
  申请人：UNIV GEORGETOWN

  公开号：WO2012138654A3

  公开（公告）日：2013-03-21
• US9085511B2
  申请人：——

  公开号：US9085511B2

  公开（公告）日：2015-07-21
• Enantioselective recognition of amines with an atropisomeric 1,8-bisphenolnaphthalene
  作者：Marwan W. Ghosn、Christian Wolf

  DOI：10.1016/j.tet.2011.07.001

  日期：2011.9

  1,8-Bis[5'(2'-hydroxy-4'-methylbiPhenyl)]naphthalene, 2, was prepared from 1,8-dibromonaphthalene and 4-methoxy-2-methylphenylboronic acid in four steps with 51% overall yield. The axially chiral anti-isomer of 2 is stable to racemization at room temperature and the free energy of activation for the conversion of the anti-isomer to the syn-form was determined as 110.0 kJ/mol at 77.1 degrees C. At submillimolar concentration, enantiopure 2 can be used as circular dichroism sensor to detect a wide range of chiral amines. (C) 2011 Elsevier Ltd. All rights reserved.